β-sitosterol | 134876-41-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: β-sitosterol
• 英文别名: Lawsaritol；(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 134876-41-8
• 化学式: C₂₉H₅₀O
• 分子量: 414.715
• InChiKey: BBTIMXAYZRWPNG-VJSFXXLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  β-sitosterol 在 吡啶 、 3,5-二甲基吡唑 、 chromium(VI) oxide 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 7-氧代-beta-谷甾醇
  参考文献：
  名称：

  Oxyphytosterols as Active Ingredients in Wheat Bran Suppress Human Colon Cancer Cell Growth: Identification, Chemical Synthesis, and Biological Evaluation

  摘要：

  Consumption of whole grains has been reported to be associated with a lower risk of colorectal cancer. Recent studies illustrated that phytochemicals in wheat bran (WB) may protect against colorectal cancer. There is a growing interest in the phytosterol contents of foods as either intrinsic or added components due to their beneficial health effects. However, little is known whether phytosterols in WB contribute the observed chemopreventative activity of the grain. In the present study, we directly purified and identified four oxyphytosterols 1-4 from sterol-enriched fraction of WB, and also successfully synthesized five sterol oxides 5-8 and 13. Using these nine compounds as references, we outlined a comprehensive profile of steroids in WB using tandem liquid chromatography mass spectrometry with electrospray ionization (LC-ESI/MSn, n = 23) techniques for the first time. Among them, three sterol oxides 13, 14, and 18 are novel compounds, and 14 compounds 3, 4, 6-11, 13, 14, 16, and 18-20 were reported in WB for the first time. Our results on the inhibitory effects of available sterol oxides 18 and 13 against the growth of human colon cancer cells HCT-116 and HT-29 showed that compounds 2-8 exerted significant antiproliferative effects, with oxysterol 8 being the most active one in both cells. We further demonstrated that four most active sterol oxides 5-8 could induce cell death through the apoptosis pathway. Our results showed that phytosterols, particularly oxyphytosterols, in WB possess significant antiproliferative properties, and thereby may greatly contribute the observed chemoprevention of the whole grain wheat.

  DOI：

  10.1021/jf506361r
• 作为产物：
  描述：

  BETA-扶桑甾醇氧化物 在 aluminum isopropoxide 、 异丙醇 作用下， 生成 24α_F-ethyl-cholesten-(4)-ol-(3α) 、 β-sitosterol
  参考文献：
  名称：

  Sterols. XXV. The Allostigmasterols and Allositosterols

  摘要：

  DOI：

  10.1021/ja01291a069

文献信息

• Optimization of conditions for biocatalytic production of stigmast-4-en-3-one
  作者：V. V. Grishko、E. M. Nogovitsina、I. B. Ivshina

  DOI：10.1007/s10600-012-0267-4

  日期：2012.7

  Pharmacologically active stigmast-4-en-3-one, the maximum formation of which (93.4 %) was achieved in the presence of n-hexadecane and palmitic acid, was produced by biotransformation of β-sitosterol (6 g/L) using rhodococcus cells. β-Sitosterol was added to the incubation medium as a mixture with β-cyclodextrin and Tween-80. The biotransformation processing conditions were optimized for β-sitosterol at high concentrations (10 g/L) using R. erythropolis IEGM 90 cells to catalyze formation of stigmast-4-en-3-one (75 %).

  具有药理活性的 stigmast-4-en-3-one，其最大形成量 (93.4 %) 在正十六烷和棕榈酸存在下实现，是通过使用红球菌生物转化 β-谷甾醇 (6 g/L) 产生的细胞。将 β-谷甾醇作为与 β-环糊精和 Tween-80 的混合物添加到培养介质中。使用红平红球菌 IEGM 90 细胞对高浓度 β-谷甾醇 (10 g/L) 的生物转化处理条件进行优化，以催化 stigmast-4-en-3-one (75%) 的形成。
• TAKASHI, MASAHIKO;YAMASHITA, ICHIRO, HETEROCYCLES., 31,(1990) N, C. 1537-1542
  作者：TAKASHI, MASAHIKO、YAMASHITA, ICHIRO

  DOI：——

  日期：——
• Oxyphytosterols as Active Ingredients in Wheat Bran Suppress Human Colon Cancer Cell Growth: Identification, Chemical Synthesis, and Biological Evaluation
  作者：Yingdong Zhu、Dominique Soroka、Shengmin Sang

  DOI：10.1021/jf506361r

  日期：2015.3.4

  Consumption of whole grains has been reported to be associated with a lower risk of colorectal cancer. Recent studies illustrated that phytochemicals in wheat bran (WB) may protect against colorectal cancer. There is a growing interest in the phytosterol contents of foods as either intrinsic or added components due to their beneficial health effects. However, little is known whether phytosterols in WB contribute the observed chemopreventative activity of the grain. In the present study, we directly purified and identified four oxyphytosterols 1-4 from sterol-enriched fraction of WB, and also successfully synthesized five sterol oxides 5-8 and 13. Using these nine compounds as references, we outlined a comprehensive profile of steroids in WB using tandem liquid chromatography mass spectrometry with electrospray ionization (LC-ESI/MSn, n = 23) techniques for the first time. Among them, three sterol oxides 13, 14, and 18 are novel compounds, and 14 compounds 3, 4, 6-11, 13, 14, 16, and 18-20 were reported in WB for the first time. Our results on the inhibitory effects of available sterol oxides 18 and 13 against the growth of human colon cancer cells HCT-116 and HT-29 showed that compounds 2-8 exerted significant antiproliferative effects, with oxysterol 8 being the most active one in both cells. We further demonstrated that four most active sterol oxides 5-8 could induce cell death through the apoptosis pathway. Our results showed that phytosterols, particularly oxyphytosterols, in WB possess significant antiproliferative properties, and thereby may greatly contribute the observed chemoprevention of the whole grain wheat.
• Sterols. XXV. The Allostigmasterols and Allositosterols
  作者：Russell E. Marker、Thomas S. Oakwood

  DOI：10.1021/ja01291a069

  日期：1937.12